I’m not ashamed to admit (ok, maybe I’m a little ashamed) that one of my (many) favorite reality shows on tv today is Millionaire Matchmaker. I haven’t seen every single episode, but amazingly enough the show teaches me a lot about myself, my relationship, and my goals in life. Patti Stanger & crew has a seemingly neverending flow of absolutely crazy, exhibistionist millionaires who want to display their crazy for all the world to see, and she has a never ending flow of offensive, sexist quips that tend to resonate in the modern dating world more than they should in 2011.

Maybe it’s the opinionated yenta inside of me, but — even when Patti offends feminists everywhere with her “girls should be girls” advice — I think she’s extremely smart about how relationships actually work, for better or worse. And, even despite often taking “logical, modern woman offense” against many of her most quotable, judgemental soundbytes, I have a bit of a girl crush on her because a lot of the time her stereotypes are right on. Granted, gender roles are less strict among us normal folk (vs the beautiful women who can chase after wealthy men, and the wealthy men that can attract beautiful women even though their looks may not be anywhere near as beautiful), but looking back on my dating life, I see how Patti would tell me I’ve gone about my relationships all wrong. I’ve been extremely lucky — my “man like” pursuit of a partner, while pushing plenty away, has landed me a guy that’s probably as close to a sole mate as I could find. Ok, so there are times I wish I had a chance to experience what it’s like to be pursued by a guy instead of being the pursuer, but as shy as I am, I never had anyone really hit on me or pursue me.

I’m not a supermodel, but I’m also not that terrible looking. I just haven’t had a “normal” dating life. And now that I’ve been in a monogmous relationship for 5.5 years, I never will — if anything, I wish i could play the “girl” role better in the relationship, but it’s too late for that. And I wouldn’t feel comfortable in that role over the long term either. If Patti had anything to say about my relationship, she’d roll her eyes. Her rule is one year of dating until a proposal, or else the girl should leave.

Well, I’m still in the relationship nearly six years later, and no ring. I’m not in a rush, but there are times I wonder if this will be the rest of my life. He says he wants to get married, so it’s not like he’s anti marriage and kids, but it’s also concerning that at this point my only control over when this happens is to leave, because I’m not allowed to propose (something both my boyfriend and Patti would agree on.) I don’t want to leave, so I’m just waiting. And I’m only a little worried that I am giving up the best dating years of my life in a dead-end relationship. But he seems to want to get married one day, and plenty of people date for many years before getting serious. For the record, if anyone proposed to me after one or two years of dating, I’d think it was too soon. It’s just now it seems like either this it, or it isn’t, and I think we both agree it is, so I don’t get why we are waiting.

One thing I know for sure, I wouldn’t be excited to be thrown back into the wild wild west of dating. I hate dating. I’ve been a bit of a serial monogomist with a few months of JDating thrown in, and I haven’t had any luck.

What is a normal dating life? I’m almost 28, and many of my friends are getting married, are married, or having kids. Clearly I’m on that path and it doesn’t look like I’ll be devating from it anytime soon. Here’s a list of all of my serious relationships in my life:

1) 6th grade. Dated a guy at Hebrew school. I’ve always liked smart guys, and smart guy he wasn’t. I don’t recall talking to him about anything in particular, and we barely hung out with each other. I recall him kissing me goodbye (just a peck) after temple, and tasting the few small cups of red wine he stuck from the onec. I was terribly insecure and disliked myself at this time (not that this has changed too much today, but I’ve come a long way given I’ve had such a long way to come). That “relationship” lasted a month or two… if you can call it a relationship.

2) 8th grade. Dated a guy who I met in the school play, he was in 6th grade. Although we didn’t speak about it at the time, he was clearly very gay. He dated me for a few weeks, then dated my friends, then dated me. We held hands and hugged. I never even kissed him. Next.

3) 8th grade summer. Dated a guy I met at the amusement park. My extroverted friend decided to flirt for me with a guy in the line for a ride. I was too scared to go on one of the bigger rollercoasters so while my friends went on it he walked around the amusement park with me and won me a prize. It was quite romantic. He later revealed to me, after we were “dating” for a few weeks, that he once had sex with a goat, or a dog. I can’t remember which. I wasn’t sure if he was joking, but the more I learned about him, the more I realized that was probably true. He was the first person I had a serious makeout session with. It was wet and sloppy and gross, and I never wanted to kiss anyone again. And he was a blonde, I’m not attracted to blondes. And, he was just not that intelligent. I mean, he fucked a goat. Or a dog. Ick.

4) 9th grade. Dated a guy my friend (same friend who set me up with the previous guy) decided I should date, who was in my drama class. He was cute, more of my type at the time, but after a month of dating, and having my friend send us letters about what to do “next” in our relationship, we realized it wasn’t working. Long term, it turns out he’s gay. I think I realized that from the start.

5) 10th grade. Briefly dated a guy who was friends with people in the alternative group at school that I quasi hung out with. He was a little geeky, but cute, and I really should have given him more of a chance, but at the time I was starting to discover my attraction to women, and thought I might be a lesbian (I’ve since determined I’m bisexual and am fine with that) — I just wasn’t interested in dating men at the time, nor did I have the self confidence needed to have a successful relationship. By the way, up until this point I was quite a prude, and hadn’t gotten very far around the bases.

6) 11th – 12th  grade. Started to date a girl who I met in chorus. She was really pretty, but the only reason we got so close in the beginning was because we both shared an infatuation with the same (female) teacher. Looking back on the whole situation, I was really looking for a strong, confident female role in my life, which was the root of my crush on the teacher, and this girl was just a hot mess. And, not to sound stuck up on the intellect issue, because I never was much of an academic, but she would rather sit around, smoke pot, and laugh at spongebob and watch cheesy horror films. We dated for two years, and it was fun and comfortable at the time. I always knew that we’d break up when I left for college (she was one year younger than me) but she was a hardcore serial monogomist and had no greater aspirations beyond finding a wife. I ran away from that as soon as I graduated. Sadly, she got into a car accident, and is now addicted to perscription pain killers (that she snorts) and, she’s an even hotter mess. It’s sad, but I’m glad we broke up. We even went to prom together, but it was never meant to be.

7) freshman year of college. Developed a crush on a female senior acting student, who was a lesbian. She was involved in the queer theater troupe that I got involved in, and eventually, through friends, it was communicated that we had a crush on each other. Our first date was quite romatic. She took me out for ice cream. Actually, this was the only time I ever really felt like the woman in a relationship. That relationship lasted for a summer and it was a fun, summer fling, but in the end we had nothing in common.

8 ) Met a guy sophomore year at a college party. He had piercing blue eyes and a very outgoing personality — one that he developed over the years as a professional magician in a family of magicians. I was attracted to him from the start — he was pretty close to my type, short, a bit nerdy, dimples, nice lips. His flirting style was cheesy but as I had never really been flirted with before I found it endearing. We dated six months, and things got serious quickly. But we never really made sense together. As much as I loved his adventerous, carefree personality, it also didn’t mesh with my more conservative, thought-out style. It was fun. He smoked, he drove fast, he had a waterbed and collected swords and owned a magic store. We dated for six months, he told me he loved me, I freaked out and broke up with him because I knew it wasn’t right.

9. Junior year of college, I decided to try out online dating. I was nervous about meeting guys in real life from online, but thought it was worth a shot. I posted an ad on craigslist that was long and completely honest. I recieved many respones from a wide variety of men, most of which were easy to put into the trash folder. One guy wrote to me, and I could tell immediately that we had a lot in common. He was also from New Jersey, enjoyed music (he sang in choirs), and — amazingly enough — was a law student in his final year at a top-tier law school in the same city where I was attending undergrad, and he went to an Ivy league for undergrad. And he was Jewish. He was older than me, but — for some reason — had never even kissed a girl yet. I fell in love with his story, but not quite with him right away. I felt comfortable with him, I just wasn’t sure we should date. I really enjoyed dating someone who was clearly more intelligent than I am — for the first time — though that came with a slew of issues from the start. The relationship went long distance when he moved for a year-long clerkship after graduating, and the year we were long distance was lovely. We had great visit weekends together. As we moved to another new city following that year, I realized our relationship was fun for what it was, but wasn’t something that made sense long term. I felt he needed to date other women before knowing what he really wanted, and could sense that although he was attracted to me, he saw me as too unmotivated and unsucessful, while his career was fast taking off. Meanwhile, he refused to pay for even a movie ticket when I was an intern and he was making a six figure salary. While I wasn’t a gold digger, his stinginess and lack of a giving nature, once I started to appreciate myself as a human being, made me want to not date him anymore. He’s a great guy for a friend, just extremely selfish. He couldn’t sleep with me in the bed, so made me sleep on the two-seater couch when I stayed over. His selfishness extended beyond our relationship, to not really caring about the problems of the world. Not that I’m an angel, but I wanted to be with someone who inspired me to be a better person, and I just felt like he was, well, a typical east coast Jew with a typical east coast Jew attitude. I kicked myself for breaking up with a jewish lawyer who liked to sing and enjoyed world travel (great on paper), it was a smart move for both of us. Last I heard, he found a woman who is much more independent than I am and a better fit for him, and I still love the guy as a friend and wish him the best. He was really my first serious relationship, and as wrong as it was for the long term, I’m glad I had the opportunity to date him. We both learned a lot about what we needed in our relationships from each other.

… this is when I had a short period of dating random guys. I didn’t want to be alone, but also really didn’t know how to date. Even before my prior relationship, despite getting dozens of responses to my craigslist ad, I didn’t end up meeting anyone else in person. This time, I went on JDate and Craigslist and went on a lot of first dates. That was an interesting experience. I was 21, fairly good looking at the time, at my thinnest, and had a handful of awkward dates. A French guy in the US for his MBA summer study  who made me an orgami paper flower the first time we met, and seemed to fall in love with me extremely quickly after I drew a picture of him. A guy who, on our second date, walked by another girl he was dating on the street on our way to dinner (awkward.) A guy who made fun of my driving on the first date, and seemed to make judgemental comments about everything I did. And a few more random men who had little in common with me, who weren’t that interested, or I wasn’t that interested. That got old fast.

10. Then, in the spring of 2006, I found my current boyfriend. I was depressed and lonely and realized that while intelligence mattered, I just wanted someone who was a good person, who would love me for who I am, who I could love in return. I threw all expectations out the window, and tried to see myself as an independant woman who didn’t need a relationship in my life. I noticed “D” during callbacks for the musical I decided to audition for, since I was feeling lonely and needed a fun, social hobby. He was tall, had a thick beard, and other than the dark hair, wasn’t exactly my type (short and clean shaven.) But something about him grabbed my attention. He looked intelligent, potentially pretentious, potentially gay, likely taken regardless; I just thought this guy is special. Throughout the rehearsal process we didn’t talk to each other. We’re both incredibly shy. I friended him on MySpace (the cool thing to do at the time) and he ended up attending a staged reading I was directing up in the city, without telling me he was coming. During rehearsals, whenever I did something silly, or made a funny comment, he always seemed to chuckle. It was adorable. We finally talked after a few drinks, and I found out that he was in a relationship with a girl he met at a party once, who lived in another state, who he never actually talked to in real life. After hearing more about this girl he was dating, it was clear to both of us that she was not right for him, and that we should be together. I heavily pursued this guy — I had to, because he was super shy, and he wouldn’t have pursued me — he’d probably still be in the relationship he was in at the time, or with another girl who was also pursuing him from the cast. So, we fairly quickly jumped into a serious relationship. We didn’t just date, neither of us could do that, we commited up front. A year or so in, I started to question the relationship, I loved that he was clearly a tender hearted, good person, with a brain to boot, but his lack of motivation (he graduated with high honors from one of the top undergraduate institutions in the country and, a year out of graduation, still hadn’t even looked for a job), and his severe introversion started to grate at me. I didn’t need a lawyer, but as I was starting to advance in my career, I thought it would be nice to date someone who was a little more motivated and career minded. Suddenly, I was in my ex’s shoes. He saw me as unmotivated and couldn’t deal. Now I had the career, and I wasn’t allowed to push him to get a job because he, like a typical guy, wanted to do everything on his own, in his own time. this hasn’t changed until this day. Now, nearly six years into the relationship, we are very much in love with each other, and nothing makes me happier than falling asleep in his arms. I can’t imagine my life without him. I can see growing old with him. Sure, we’ll never be rich, and we might not even be stably in the upper middle class where I grew up, but something tells me this is right… this is what life is about. It’s wonderful to feel loved for who I am, and to love that deeply and honestly in return.

Still, I’m scared. I don’t know what the future holds. While you can’t predict the future, one thing I feel strongly about is saving enough money to handle whatever life throws at you. So far, I’ve saved over $130k on salaries of $25k, $35k, $50k, $60k, and $90k. I could have saved more, but I’m proud of myself for putting that much money aside before turning 28. My goal is to have at least $200k in the bank by the time I turn 30. My boyfriend, on the other hand, doesn’t have a retirement account to speak of, or much in term of savings. He’s never had a full time job, though he’s worked on contract for a non-profit for a while now, and he hasn’t asked for a raise, he just got a small one when he asked to quit, and they didn’t want him to. I don’t know if it’s ok to care about this or not, or how much to care. He says he is going back to grad school to become a high school teacher, and he’s been talking about going back to school for years. I’d be happy with him being a teacher — he’s well suited for that job, he’d be great at it, and he’d never have to negotiate for a raise at a public school where the salary is set. Is it wrong to think about this and consider it when looking at who you’re going to spend your life with? Where is the line between being a gold digger and being a rational modern woman? I can’t tell.

My good friend, who I grew up with, dreamed of finding a wealthy guy who would buy her a large house, and give her the flexibility to be a school teacher and a full-time mother at a fairly young age. She found her man and she got her house and she had her beautiful diamond engagement ring and a date set for the wedding. She seemed set for life — then she found out her fiance cheated on her by finding closeup photos of another woman’s privates on his cell phone, and confronted him about this. She tried hard to deal with the jealously, to accept his apologizes, but she couldn’t forgive him. So she left him, and left the house, and left the life she had dreamed of, still dreaming of finding another man to fullfill this dream. She’s dated a few guys, a few long term, but her relationships since have not gone anywhere. I was talking to her this weekend, and she’s so sad. She’s gourgeous, and can get men easily, yet in her works she can’t “keep them.” She never thought of being a career-minded woman, as her income as a teacher would only be supplemental to her husband’s sizable six-figure salary.

I wouldn’t want to spend my life with a guy who is all about his career, so I really shouldn’t complain or even worry. My role in this relationship is clearly as the breadwinner, and although I may freak out over knowing that I can’t take a few years off to be a full-time mother, I’m not sure I’d even want to do that. I like making money. I like knowing that I can take care of myself. And when I have kids, making money will have even more significance when it is for my family. So what’s to worry about? Why do I need to be jealous of the women on Millionaire Matchmaker who don’t mind continuing to write the definition of gold digger, who want to have a life in a traditional “woman” role? Is that so wrong? Is that what I should want, or will want later in life, when it’s too late to go back?

Living in Silicon Valley, there are a lot of guys here, and while a lot of the good ones are taken, there are still quite a few eligible bachelors — engineers and entrepreneurs — who could, even without Patti’s help, put me in line for a more financially stable life. It’s not to say any of them would like me, or that I’d like them, or that I’d ever find a worthwhile relationship, it just leaves me wondering what life could be, should be, and will be — because you only have one life, and who you marry, or don’t marry, is no small decision in the story of one’s life.